20/20: An #AskJakeAnything to Guide You into the New Year

What I’ve noticed since starting #AskJakeAnything is people are asking questions that a lot of other sales professionals have and have probably wondered about for years. I’ve had some very similar questions throughout my career myself. Sometimes I had a mentor at the time who could give me the answer, sometimes it took years of experience to figure out on my own. 

These 20/20 questions and answers are split up into a few categories so you can easily find some of those burning questions you’ve had in 2019 that I hopefully answer going into 2020. Topics vary from cold calling, to prep, career moves, and an interesting one on how I maintain my high energy for what I do on an ongoing basis. You’ll never guess.

Categories Covered:

1. Sales Strategy
2. Tech
3. Sales Tactics
4. Career Development
5. LinkedIn
6. Tic Toc
7. Life

Sales Strategy

Q. Chris Walker - Why do you think people aren’t prepping?

A. Hubris. Our brains tend to stereotype things, so for a lot of sales people, after they’ve run 10-20 sales meetings, they think they’ve gotten the process and the conversation down cold, and prepping is no longer necessary.

It’s also these same sales people who aren’t prepared for objections, or when someone brings something up they hadn’t thought of, the rep doesn’t know how to answer. 

I’m a prep monster. If I’ve got a big meeting coming up, I try to get my V1 of whatever that prep is a week in advance. Most people only ever get to 80% prepared because they don’t take the time to prep. If you get to that 80% a week in advance, then you have time to review, iterate, and get closer to 95% prepared.

Q. Ky Shaw - What kind of success have you seen building out Rev Ops teams?

A. First, let’s define Rev Ops for all my friends out there who aren’t quite sure. Revenue Operations is a group of individuals who are looking at the revenue operations of your team end to end. What are the pain points and where are things falling off? Think of them as your funnel ninjas looking at everything that is happening.

A Rev Ops team is absolutely critical as you scale so you have a person in place that can look at everything from first touch point in Marketing to churn of customers. Once you get to about 20-30 people on your Sales team, Revenue Operations can make a big difference for your organization.

Q. Chris Watson - What are the most important questions that a prospect needs answered before they consider purchasing a product or service?

A.

1. Why me? What’s in it for me as an individual and not just the company? 
2. Why now? Why do they need to do this now? What’s the compelling event? Why should they make an investment in your product or service right now versus waiting until the next quarter? 
3. Why you? Why should the prospect pick you? How do you stand out from the competition and how are you different?
4. What happens at implementation? A lot of the reasons that your deals might ghost is people get nervous about what happens after they buy. 

John Barrows has a framework around the first three, which are pretty universal, but the fourth is becoming more and more important to the conversation. If you’re not walking people through the implementation process, they might get behind a closed door and start asking, “Who is going to implement this?” If no one steps up or has the bandwidth, your deal will fall through.

Q. Kevin Mulrane - Considering how buyers are evolving, what are the best ways to bridge the sales and marketing gap and create better alignment?

A. It’s really a very simple answer. Marketing and Sales have to be compensated on the same things - mostly. 

Both teams should be compensated on late stage pipeline or revenue. Anything other than that will continue to create a divide. Where “mostly” comes into play, is Marketing shouldn’t only be judged on revenue because they’re also responsible for the brand and creativity component of the business that’s also very important. But if we’re talking about how to create better alignment between the two, then both teams have to be focused on revenue and compensated the same.

Tech

Q. Sam Best - Jake, what would you say your top sales weapons are in the space today? If you could build out the ideal sales tech stack, what would it be?

A. There are thousands of tech options out there and the options are only going to grow. What business need to be deliberate about building a tech stack that covers the full funnel or loop of a sale. That means,

1. Clean data or a clean database
2. A way to utilize that data to engage and interact with people in an effective manner
3. A way to understand what happened when you took the actions that you took

Therefore, I’m looking at DiscoverOrg and Zoominfo for richer, cleaner data. I’m looking at Outreach and SalesLoft for middle funnel and sales engagement. And for reporting there are tools like Collective[i], People.ai, InsightSquared, Clari, etc. 

At the end of the day, this last piece of tech is what’s going to tell you how to optimize. Did you have the right data or is that where things broke? What happened when you took these actions? What actually lead to a deal getting done? 

There are a few other options that are icing on the cake such as Gong, ExecVision, and Chorus that are good for coaching. And then there is LinkedIn Sales Navigator that’s a must for lead gen.

Q. Amy Volas - Jake, what’s the biggest opportunity for tech that you see sales people getting bogged down with?

A. The biggest thing to understand is tech is supposed to work for you not do your job for you. Too many people are looking at technology to automate the work. Technology can automate the follow-up and remembering to do similar tasks, but you still have to push your creativity and human understanding into the technology. That is, think about why you are doing something a certain way. Did it work? Did it not work? Technology can help you track these results but again, technology’s role is not to do the work for you. 

“Send all” is not an option. Automating a generic follow-up to a person you just had a meeting with that has not relevant information about the conversation is not an option. 

You must incorporate creativity and a human touch with the technology you use - unless you want the tech to replace you.

Sales Tactics

Q. Max Hart - What are the fundamental differences and/or things to be aware of when selling a piece of software versus a service? To keep it simple, if you’re selling into the same account, what things do you need to do differently to close the deal. (Jake is selling accounting software to Company X, while Max is selling consulting services to Company X)?

A. Candidly, the process isn’t that different. Whether you’re selling software or a service, there has to be a compelling event or reason for the buyer to move forward. There has to be something happening in their business for them to want to move forward.

The buyer has to feel like you actually understand their challenges and you’ve got a plan to help them solve the challenge and a plan to help them implement the solution and go live. It’s the same for a product or service.

The only difference is with service companies, in which people and not software is the solution. It’s not that different on the front end of the funnel, but how you handle fulfillment is going to look different. A good sales process is a good sales process and that includes key milestones for the buyer such as discovery, worldview alignment, and driving momentum, which again, is the same for selling products and services.

Q. @bmarzo18 (Instagram) - How do you put urgency when following up with prospects via text?

A. Text emails and messages are the easiest thing to ignore. People will hit delete in a second and not think twice. Using multimedia and not just text is what’s going to help you stand out. If someone goes dark or you’re trying to get a hold of someone, try sending them a personalized video. There are multiple companies who can help you do this such as Videolicious and Vidyard. You can also add video to LinkedIn messages if the other person is a first degree connection.

Try using video in 2020 if you’re trying to drive more urgency or to give more color to your product or service. If not, the key is going back to the basics. 

I’ve mentioned the importance of compelling events a couple of times in this article. If you don’t have a compelling event to tie back to and a way to remind a buyer why it’s important to move forward now, you’re going to keep struggling to close. For example:

“Hey Courtney, you said that X needed to be done by January 1 for the team to then do Y by February 1st. I understand things change, let’s have a conversation about it.” 

Tying it back to their own words and a compelling event is one of the best tactics you can use to drive urgency.

Q. @cooperbaggs (Instagram) - Hey Jake, what’s your preferred method or strategy when conducting a cold call with the intent of securing a meeting?

A. People like to see themselves in the mirror. Don’t cold call someone with the into tell them all about you. Talk to them about them.

I always prepare for a cold call by learning about what exactly the company does and who does my company work with that is very similar to the company I’m cold calling. 

1. What sub-industry are they in that I work with? For example, I need to know if they are an industrial manufacturing company not just a manufacturing company.
2. What size company are they? If they are a 100 person software company, they’re not going to care if I start talking about my work with a large company like Facebook.
3. If possible, do I work with a company in the same sub-industry, about the same size, and also the same geolocation? 
4. Lastly, what pain points do I know this person is mostly likely going to have in their job based on similar companies and people I’ve worked with?

If I know those four things - sub-industry, company size, location, and pain points - then I’m going to exponentially increase my number of meetings set. 

Q. Samuel DeJarnett - What about with year end closings for sales teams? Any advice for lead gen teams when the prospect says, “We can look at this in the new calendar year/fiscal year”? How do you get them into the sales cycle? 

A. If you want people to close this year you have to understand their compelling event for buying before 2020. This is where a lot of people fall flat. They are unable to understand or don’t uncover WHY. 

Buyer: We need to hire 25 people. 

Sales: Why now? 

Buyer: We’ve got a new office we’re trying to open up in March. 

Sales: What’s our lead time to hire for that role? 

Buyer: It’s usually 3 months.

Sales: In that case, we have to get started in January (Meaning they have to buy in December.)

If you don’t have a compelling event that is driven by the customer, it’s really hard to push people over the edge other than using some junky end of year discount.

If you don’t know their compelling event, go back and get it. 

Career Development

Q. Anonymous - How do you motivate your team to push a new product or service besides from just creating a higher incentive payout.

People have to understand the why. They struggle with change if they don’t have it. 

If you can help your team understand how this new product or service is going to move the needle, why it’s important, how it’s progressing with the industry, and why this change needs to be made now to stay on top, it will make a huge difference in motivating your team.

Q. Anonymous - How do you teach coachability to your team?

First, you need to understand that each individual is at a different place in their career and experience. Some people you need to teach, some people you need to coach, and some people you need to mentor.

People who need to be taught are very early in their career and they may not even understand what you’re talking about means. You’re going to need to teach or explain the skill.

People who need to be couched already have the basics down but have gaps here and there.

People who need to be mentored have the experience, the raw potential, and pick up new skills to layer on top of the skills they already have quickly.

The important thing to think about here is making sure that you meet people where they are experience-wise.

Q. Anonymous - How do you rate sales jobs that don’t pay OTE but instead pay a high-base salary?

A. This is an interesting question. It’s been kind of the anti-sales question for a long time, but I foresee a lot more companies starting to go this way. It’s the same as when you look at other countries and how they pay their servers. The U.S. has always been a very “incentive” laden culture. But as the job of sales changes and transforms and becomes more about project management and helping people, there could be an argument that instead of compensating the seller, we inspire and motivate them in other ways to just do the right thing for the customer. I’m not saying we should do away with OTE or some type of bonus altogether, but put less of an emphasis on it.

The reason why we like compensation with incentives today is because it’s easy. It’s much easier for the employer to motivate sellers with dollars than intrinsically as a human. But, as the job of sales changes, we may see more companies moving to higher base salaries.

Q. Sai Patel - Jake, I’m thinking about getting my MBA to open up more job opportunities. Is it worth it?

Yes, in two scenarios:

1. If you go to a prestigious or Ivy League school, it’s absolutely worth it to be a part of that network. If you go to one of these top schools and get an MBA, it’s going to be pretty tough to fail.
2. If you’re deliberate about why you want to get an MBA. Don’t go because you think it’s going to get you a new job. The data shows that less and less people are requiring MBAs. Go to grad school because you want to fill some type of skill gap. You want to help elevate your own game for yourself, and not because you expect another job opportunity.

Q. Nikki Ivey - What are the first/best steps to take after being fired from a sales job?

A. I can answer this one, because I’ve been fired from a sales job. The first thing to do is listen to Train in your car alone and cry. That’s what I did. I’m not too afraid to admit it. I also thought that my life was over and getting fired wasn’t something that happened often. Throughout life I figured out that it happens all the time. 

The first step is to take a moment for yourself. That’s my very first piece of advice. It’s OK to have a pity party.

The next important step is to take stock of what you want to do next and be smart about it. Figure out what’s the next best move, what culture do you want to be a part of, and what are you truly amazing at because you are amazing and capable of way more than you think.

… and then move forward. 

LinkedIn

Q. Benjamin Pittman - Why does everyone on LinkedIn type with spaces between each sentence?

A. My honest best guess is it’s easier to read. If you write a big, chunky paragraph, I just don’t think people are going to want to read it. Adding spaces tricks them into thinking that it’s less copy and will take them less time to read. 

It also almost creates a dramatic pause…

This is a technique that a lot of people have just started to do naturally, but it’s a good callout, Benjamin.

Q. Anonymous - Jake, I’ve been working on my personal brand, posting on LinkedIn, and really starting to see results. However, my team makes fun of me for it and my boss thinks it’s silly and doesn’t want to implement it across our team. I’m hitting all my numbers, getting recognition, building better reporte with my prospects, and I’m getting noticed out and about, but my team still thinks it’s silly. What do I do?

A. You have to do what the trends and the market say you should do. Period. 

You cannot help that people are going to be behind the times. When you are thinking about what your truth is, if it feels right, just keep doing it. I can tell you that some of the people on my team, that are very close to me, and have worked with me for a long time, had their doubts and also made fun of me. But trust me, after 9-12 months. They all come around.

What you’re doing is working, and the market decides what works and what doesn’t, not your coworkers or boss who haven’t caught up. If the market is telling you it’s right - keep doing it.

Tic Toc

Q. Lorenz Esposito - How will Tic Toc be leveraged for employer branding strategies?

We’re still in the very early stages of Tic Toc, and it’s tough to know if it’s just going to die off like Vine. But we are starting to see companies in B2C and the NFL starting to use it which are indicators of possible success. 

If you want to be a leading brand early on who’s fun, different, or interesting on Tic Toc, the key is to still be relevant. You have to know what the audience on Tic Toc is looking for and if your content is going to be relevant to them.

I think getting Tic Toc is great, and my company is thinking a lot about some cool stuff we can do in 2020, but you have to think about your audience first.

Life

Q. Joel Parent - You seem to have great energy. What do you do to maintain your energy on an ongoing basis?

Here’s the thing. Everyone has ebbs and flows, no matter if you’re Gary V or Richard Branson. Early in my career, I developed a “trigger” to help me. It started with sales calls. I knew I didn’t have the ability to keep up that energy 24/7. It would have been impossible. Instead, I figured out that you have to have the ability to turn it off and on when needed. For me, it was a light switch mechanism. It’s a little weird, but I literally visualize a light switch to pull that extra umph out when needed.

It’s key to realize that you don’t have to maintain optimal energy 24/7, but also, if you’re doing what you’re passionate about, it becomes less draining.  If you find something that you enjoy doing, it’s easier to get excited about it so you’re flipping that switch less and less. 

Q. Amy Quick - What inspires the passion behind what you do day in and day out?

A. The key is aligning what you do and being very honest with yourself about what you’re good at and what you’re not good at. 

I’ve had to do a lot of different things as the CEO of a startup, because I’ve had to do them. Over time, I’ve realized that the things I’m not particularly great at or are a mental drain on me, most likely there is somebody else who is better suited. I think a big piece of continuing to be passionate about what you do is continue to be very honest with yourself about what you’re not passionate about and just because you can do something, doesn't mean you should. Always try to align what you’re doing day-to-day with your passions.